New synthetic reactions. Synthesis of cyclobutanes, cyclobutenes, and cyclobutanones. Applications in geminal alkylation

BM Trost, DE Keeley, HC Arndt…

Index: Trost,B.M. et al. Journal of the American Chemical Society, 1977 , vol. 99, p. 3088 - 3100

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Citation Number: 99

Abstract

Abstract: The chemistry of the adducts of 1-lithiocyclopropyl phenyl sulfide to aldehydes and ketones is reported. Treatment of these compounds with p-toluenesulfonic acid under anhydrous conditions or the Burgess reagent yields l-phenylthiocyclobutenes, which may be hydrolyzed to cyclobutanones, desulfurized to cyclobutanes, or thermalized to dienes. Rearrangement to cyclobutanones can be achieved under four sets of conditions:(1) ...